Over the past 20 years, separate and distinct synthetic methodologies have been developed by Sharpless et al. for the vicinal hydroxyamination of olefins. There are three major groups of oxyamination procedures which produce aminoalcohols (Sharpless et al. J. Am. Chem. Soc. 1975, 97, 2305; Sharpless et al. J. Org. Chem. 1978, 43, 2628; Sharpless et al. J. Org. Chem. 1980, 45, 2257), hydroxysulfonamides (Sharpless et al. J. Org. Chem. 1976, 41, 177; Sharpless et al. J. Org. Chem. 1978, 43, 2544; Sharpless et al. J. Org. Chem. 1979, 44, 1953; Sharpless et al. Org. Syn. 1980, 61, 85) or hydroxycarbamates (Sharpless et al. J. Am. Chem. Soc. 1978, 100, 3596; Sharpless et al. J. Org. Chem. 1980, 45, 2710; Sharpless et al. U.S. Pat. Nos. 4,871,855; 4,965,364; 5,126,494; EP 0 395 729). Each oxyamination procedure has unique reaction conditions and includes variations in solvents, auxiliary salts, nucleophiles, temperature, stoichiometric v. catalytic amounts of osmium species and stoichiometric v. catalytic amounts of ligand. Each procedure is highly dependant on the nature of the substrate and possesses unique properties which afford different yields, chemoselectivities, stereoselectivities, regioselectivities and enantioselectivitive outcomes.
What is needed is a method for regioselectively and enantiomerically catalyzing the asymmetric aminohydroxylation of cinnamate based olefinic substrates using carbamate oxidants for producing aryl serines.